“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety of vital biological processes. Access to unique and homogeneous carbohydrate materials is important to understand their physical properties, biological functions, and disease-r...

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Bibliographic Details
Published in:Chemical reviews 2018-09, Vol.118 (17), p.8025-8104
Main Authors: Kulkarni, Suvarn S, Wang, Cheng-Chung, Sabbavarapu, Narayana Murthy, Podilapu, Ananda Rao, Liao, Pin-Hsuan, Hung, Shang-Cheng
Format: Article
Language:English
Subjects:
Biological activity
Biological properties
Carbohydrate Conformation
Carbohydrate Sequence
Carbohydrates
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Catalysis
Chemical synthesis
Chemistry Techniques, Synthetic - methods
Chemists
Coupling (molecular)
Domains
Glycan
Glycosylation
Molecular biology
Oligosaccharides
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Organic chemistry
Physical properties
Polysaccharides - chemical synthesis
Polysaccharides - chemistry
Protection
Saccharides
Stereoisomerism
Stereoselectivity
Sugar
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Summary:Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety of vital biological processes. Access to unique and homogeneous carbohydrate materials is important to understand their physical properties, biological functions, and disease-related features. It is difficult to isolate carbohydrates in acceptable purity and amounts from natural sources. Therefore, complex saccharides with well-defined structures are often most conviently accessed through chemical syntheses. Two major hurdles, regioselective protection and stereoselective glycosylation, are faced by carbohydrate chemists in synthesizing these highly complicated molecules. Over the past few years, there has been a radical change in tackling these problems and speeding up the synthesis of oligosaccharides. This is largely due to the development of one–pot protection, one–pot glycosylation, and one–pot protection–glycosylation protocols and streamlined approaches to orthogonally protected building blocks, including those from rare sugars, that can be used in glycan coupling. In addition, new automated strategies for oligosaccharide syntheses have been reported not only for program-controlled assembly on solid support but also by the stepwise glycosylation in solution phase. As a result, various sugar molecules with highly complex, large structures could be successfully synthesized. To summarize these recent advances, this review describes the methodologies for one-pot protection and their one-pot glycosylation into the complex glycans and the chronological developments associated with automated syntheses of oligosaccharides.
ISSN:0009-2665
1520-6890
DOI:10.1021/acs.chemrev.8b00036